Methylsalicylat

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H318：Verursacht schwere Augenschäden.

• Sicherheit

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P270：Bei Gebrauch nicht essen, trinken oder rauchen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Methyl salicylate Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  FARBLOSEODER GELBE BIS ROTE, öLIGE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.

• CHEMISCHE GEFAHREN

  Reagiert mit starken Oxidationsmitteln und starken Basen.

• ARBEITSPLATZGRENZWERTE

  TLV nicht festgelegt (ACGIH 2004). MAK nicht festgelegt (DFG 2004).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.

• INHALATIONSGEFAHREN

  Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Die Substanz reizt die Augen und die Haut. Möglich sind Auswirkungen auf das Zentralnervensystem mit nachfolgendem Schock und Tod. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.

• LECKAGE

  Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R36/38:Reizt die Augen und die Haut.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.

• Beschreibung

  Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic ester that is naturally produced by many species of plants. Some of the plants which produce it are called wintergreens, hence the common name. This compound is used as a fragrance. It is also found in liniments (rubbing ointments).

• Chemische Eigenschaften

  Methyl Salicylate is the main component of wintergreen oil and occurs in small quantities in other essential oils and fruits. It is a colorless liquid with a characteristic wintergreen-like odor. May be prepared by extraction from natural sources; or by esterification of salicylic acid with methanol.

• Chemische Eigenschaften

  Wintergreen is an evergreen shrub with slender, creeping stems, assurgent, flowering branches with toothed leaves clustered at the top, white, bell-shaped flowers blossoming July to August, followed by red berries (checkerberries). The plant grows extensively in the woods of Canada and the United States (Pennsylvania). The leaves are harvested between June and September. Wintergreen has an aromatic odor and flavor similar to methyl salicylate.

• Occurrence

  Numerous plants produce methyl salicylate in very small amounts. Some plants, such as the following, produce more:
  Some species of the genus Gaultheria in the family Ericaceae, including Gaultheria procumbens, the wintergreen or eastern teaberry;
  Some species of the genus Betula in the family Betulaceae, particularly those in the subgenus Betulenta such as B. lenta, the black birch;
  All species of the genus Spiraea in the family Rosaceae, also called the meadowsweets.
  This compound is produced most likely as an anti-herbivore defense. If the plant is infected with herbivorous insects, the release of methyl salicylate may function as an aid in the recruitment of beneficial insects to kill the herbivorous insects.Aside from its toxicity, methyl salicylate may also be used by plants as a pheromone to warn other plants of pathogens such as tobacco mosaic virus.

• Verwenden

  Potent inhibitor of ornithine decarboxylase

• Verwenden

  Methyl salicylate is used in high concentrations as a rubefacient in deep heating liniments (such as Bengay) to treat joint and muscular pain. Randomised double blind trial reviews report evidence of its effectiveness that is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counter-irritation. However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.
  It is used in low concentrations as a flavoring agent (no more than 0.04 %; it is toxic). It is also used to provide fragrance to various products and as an odor-masking agent for some organophosphate pesticides . If used excessively, it can cause stomach and kidney problems.
  Methyl salicylate is among the compounds that attract male orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.

• Verwenden

  Methyl salicylate occurs in the leaves ofGaultheria procumbens L. and in the barkof Betulaceae. It is produced by esterificationof salicylic acid with methanol. It is used inperfumery and as a flavoring agent.

• Verwenden

  In high concentrations as a rubefacient in deep heating liniments (such as Bengay) to treat joint and muscular pain. Randomised double blind trial reviews report evidence of its effectiveness that is weak, but stronger for acute pain than chronic pain, and that effectiveness may be due entirely to counter-irritation. However, in the body it metabolizes into salicylates, including salicylic acid, a known NSAID.
  In low concentrations as a flavoring agent (no more than 0.04%; it is toxic).
  providing fragrance to various products and as an odor-masking agent for some organophosphate pesticides. If used excessively, it can cause stomach and kidney problems.
  Attracting male orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.
  Clear plant or animal tissue samples of color, and as such is useful for microscopy and immunohistochemistry when excess pigments obscure structures or block light in the tissue being examined. This clearing generally only takes a few minutes, but the tissue must first be dehydrated in alcohol.
  A mint flavoring in some kinds of chewing gum and candy, as an alternative to the more common peppermint and spearmint oils. It can also be found as a flavoring of root beer. It is also a potentially entertaining source of tri boluminescence ; when mixed with sugar and dried, it gains the tendency to build up electrical charge when crushed or rubbed. This effect can be observed by crushing wintergreen Life Savers candy in a dark room.

• Verwenden

  Methyl salicylate is an organic ester that is commonly produced naturally by wintergreens. Methyl salicylate is utilize as a anti-herbivore defense system in various plants that produces it. Methyl sa licylate is also used in high concentrations as a rubefacient to treat joint, muscular pain and acute pain. Methyl slicylate is also used as a flavoring agent and often used to provide fragrance to pr oducts.

• Definition

  ChEBI: Methyl salicylate is a benzoate ester that is the methyl ester of salicylic acid. It has a role as a flavouring agent, a metabolite and an insect attractant. It is a benzoate ester, a member of salicylates and a methyl ester. It is functionally related to a salicylic acid.

• Vorbereitung Methode

  Methyl acetate, a novel acyl acceptor for biodiesel production has been developed, and a comparative study on Novozym 435-catalyzed transesterification of soybean oil for biodiesel production with different acyl acceptors has been studied (Noureddini et al., 2005).
  
  Figure 1 shows the effect of the molar ratio of methanol to sunflower oil on the methyl ester yield for catalytic (3% CaO) transesterification in supercritical methanol at 523 K.

• synthetische

  Methyl salicylate can be produced by esterifying salicylic acid with methanol. Commercial methyl salicylate is now synthesized, but in the past, it was commonly distilled from the twigs of Betula lenta (sweet birch) and Gaultheria procumbens (eastern teaberry or winter green).

• Composition

  The leaves of wintergreen are reported to contain arbutin, caffeic acid, ericolin, ferulic acid, gaultherase, gaultheric acid, gaultherin, gentisinc acid, methyl salicylate (5445 to 7920 ppm) o-pyrocatachuic acid, p-coumaric acid, p-hydroxybenzoic acid, primverose, protocatachuic acid, syringic acid, tannic acid, tannin, tricontane and vallininc acid.

• Aroma threshold values

  Detection: 40 ppb

• Taste threshold values

  Taste characteristics at 10 ppm: sweet, salicylate and root beer with aromatic and balsamic nuances

• Synthesis Reference(s)

  Canadian Journal of Chemistry, 61, p. 688, 1983 DOI: 10.1139/v83-127
  The Journal of Organic Chemistry, 40, p. 3649, 1975 DOI: 10.1021/jo00913a007
  Tetrahedron Letters, 37, p. 153, 1996 DOI: 10.1016/0040-4039(95)02120-5

• Allgemeine Beschreibung

  Colorless yellowish or reddish liquid with odor of wintergreen.

• Air & Water Reaktionen

  Insoluble in water.

• Reaktivität anzeigen

  Methyl Salicylate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Birch-Me is incompatible with oxidizers. Birch-Me is also incompatible with strong bases. Birch-Me may react with iron salts.

• Hazard

  Toxic by ingestion; use in foods restrictedby FDA, lethal dose 30 cc in adults, 10 cc in chil-dren.

• Health Hazard

  Methyl salicylate is a highly toxic compound.The toxic symptoms in humans include nausea, vomiting, gastritis, diarrhea, respiratorystimulation, labored breathing, pulmonaryedema, convulsions, and coma. Ingestion of15 to 25 mL of this compound may befatal to humans. Application of the liquidon the skin and eyes produced severe irrita tion in rabbits. Oral, subcutaneous, or der mal administration of methyl salicylate intest animals produced specific developmen tal abnormalities affecting the eyes, ears, andcentral nervous system
  Toxicity of this compound is relativelymore severe in humans than in many com mon laboratory animals. The oral LD50 values in test animals were within the range800–1300 mg/kg.

• Brandgefahr

  Methyl salicylate is combustible.

• Flammability and Explosibility

  Non flammable

• Kontakt-Allergie

  This anti-inflammatory agent is found in a wide number of ointments and can induce allergic contact dermatitis.

• Biochem/physiol Actions

  Methyl salicylate plays an important role in fruit ripening. It is known to attract natural enemies of herbivores. MeSA inhibits the activity of aminocyclopropane-1-carboxylic acid synthase (ACC synthase) and aminocyclopropane-1-carboxylic acid oxidase (ACC oxidase) in plums and tomatoes, it can inhibit fungal infections and reduce chilling injury symptoms in fruits like pomegranates. This oil of wintergreen is of great interest in the tobacco industry as a flavorant. It has counter irritant and anti-inflammatory effects.

• Sicherheit(Safety)

  In pure form, methyl salicylate is toxic, especially when taken internally. A single teaspoon (5ml) of methyl salicylate contains 7g of salicylate, which is equivalent to more than twenty- three 300 mg aspirin tablets. The lowest published lethal dose is 101 mg / kg body weight in adult humans , (or 7.07 grams for a 70 - kg adult). It has proven fatal to small children in doses as small as 4 ml.[6] A seventeen-year- old cross - country runner at Notre Dame Academy on Staten Island, died in April 2007, after her body absorbed methyl salicylate through excessive use of topical muscle-pain relief products.
  Most instances of human toxicity due to methyl salicylate are a result of over-application of topical analgesics, especially involving children. Some people have intentionally ingested large amounts of oil of wintergreen. Salicylate, the major metabolite of methyl salicylate, may be quantitated in blood, plasma or serum to confirm a diagnosis of poisoning in hospitalized patients or to assist in an autopsy.

• Sicherheitsprofil

  Human poison by ingestion. Moderately toxic to humans by an unspecified route. Moderately toxic experimentally by intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: flaccid paralysis without anesthesia, general anesthesia, dyspnea, nausea, vomiting, and respiratory stimulation. Experimental reproductive effects. A severe skin and eye irritant. Ingestion of relatively small amounts has caused severe poisoning and death. Combustible liquid when exposed to heat or flame; can react with oxibzing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

• Synthese

  By esterification from natural sources; by esterification of salicylic acid with methanol

• Carcinogenicity

  Available data suggest that methyl salicylate is not carcinogenic.

• läuterung methode

  Dilute the ester with Et2O, wash with saturated NaHCO3 (it may effervesce due to the presence of free acid), brine, dry MgSO4, filter, evaporate and distil it. Its solubility is 1g/1.5L of H2O. The benzoyl derivative has m 92o (b 270-280o/120mm), and the 3,5-dinitrobenzoate has m 107.5o, and the 3,5-dinitrocarbamoyl derivative has m 180-181o. [Hallas J Chem Soc 5770 1965, Beilstein 10 IV 143.]

• Toxicity evaluation

  Oral LD50 values (mg/kg) for mouse, rat and rabbit are 1110, 887 and 1300, respectively. Oral LD50 values for child and adult human (mg/kg) are 228 and 506, respectively. Topical methyl salicylate generally rarely causes systemic toxicity, but it can be absorbed by the skin leading to stimulation of the central nervous system respiratory center, disturbance of lipid and carbohydrate metabolism, and disturbance of intracellular respiration. Severe poisoning can lead to acute lung injury, lethargy, coma, seizures, cerebral edema, and death. In the case of salicylate intoxication, treatment includes general supportive care, purification of the gastrointestinal tract with activated charcoal in the case of ingestion of salicylic acid, and monitoring of serum salicylic acid concentration. Bicarbonate infusion or hemodialysis can be used to enhance the elimination of salicylic acid.

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